In this episode of Outreach With Reggie, Reggie Holloway unpacks the quiet disappointment many people feel after reaching milestones they were told would bring happiness — graduating, landing the job, checking the box, or “doing everything right.” We dive into the social impact of these experiences and how success without a sense of purpose can feel hollow, reflecting on themes of social justice and activism.

Explore why fear keeps people stuck after failure, why so many New Year’s resolutions collapse within weeks, and how societal systems shape our definitions of success. Reggie also shares personal insights into the pressure to perform, social comparison, and the challenge many face when they stop believing they can rise above systemic limitations or their past.

This episode features a powerful discussion on foster youth and post-s ...